


Hardest Part is Letting Go

by raisedufromperdition



Category: Supernatural
Genre: Character Death, Dean Winchester Actually Deals With Feelings, Domestic Castiel/Dean Winchester, Domestic Fluff, Established Castiel/Dean Winchester, Established Relationship, Explicit Language, Fluff, M/M, Smut, alternative universe
Language: English
Status: In-Progress
Published: 2021-03-16
Updated: 2021-03-24
Packaged: 2021-03-25 10:14:45
Rating: Mature
Warnings: Major Character Death
Chapters: 3
Words: 7,412
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30087549
Author URL: https://archiveofourown.org/users/raisedufromperdition/pseuds/raisedufromperdition
Summary: Upon his diagnosis of a terminal illness, Dean vows to spend the rest of his short life with Cas by his side, completing his bucket list while learning what it really means to live and love.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Comments: 6
Kudos: 12





	1. It's Not the Song, it is the Singing

Dean had never been a romantic – that was always Cas and his extravagant date planning. It was incredibly endearing, but Dean just wasn’t one of those people that cared about that kind of stuff. He loved it because Cas loved it. Funny how a terminal illness can change someone.

It was one year earlier, just after Dean’s thirtieth birthday. Recently he hadn’t been feeling well. His energy level was low, and the sweeping waves of nausea became all too familiar. While low energy wasn’t exactly uncommon for him, this was different. Dean barely had the energy to get out of bed. At first, Cas assumed it was some kind of flu, so they spent the day in bed watching old western movies and eating soup. It was a few days later when Dean realized something wasn’t quite right. Along with the loss of energy, came the loss of appetite, and consistent headaches. Dean hid it well, though. After all, he didn’t want to worry Cas or Sam. So he pretended everything was fine for the next few weeks and almost convinced himself he was starting to feel better. He thought that with time it would eventually go away. However, it ws quite the contrary.

One morning Dean awoke at his worst with a sharp, hot pain in his head; it was by far the most excruciating thing he has ever experienced. Biting down on his pillow, he screamed. He screamed until his voice was hoarse, just trying to release some of the pressure in his head. His nails dug into the blankets, begging for the pain to end. Soon darkness took over his vision and he drifted into blissful unconsciousness, away from the pain.

The next time Dean woke up he was in a hospital, with an IV hooked to his right arm and an oxygen tube in his nose. The fluorescent lights were harsh, highlighting the deep bags under his eyes. At least the pain in his head had subdued. His vision became sharper as the flog from the drugs cleared. Dean looked around the room, noting the ‘get well soon’ balloons and cards that littered the room. To his left was a card with a scrawl so ineligible it could only be identified as Sam’s attempt at handwriting. But the thing that caught his attention was Cas, sitting in this stiff chair next to his bed, his head resting on his hands.

Dean shot up, suddenly alarmed as he remembered the events that led to him being here. He sat up, pulling at the IV, panic rising in his chest. His hate for hospitals was heightened and all he could focus on was getting out of here. But then Cas’s head shot up to the sounds of Dean rustling in bed. He scooted his chair closer to the bed, resting his hand on Dean’s.

Dean frowned as he observed his boyfriend’s face. His nose was runny, and his eyes were pink and swollen. He had been crying. It was enough to stop Dean’s frantic movements as his heart rate increased. Cas very rarely cries, and when he does it’s for good reason. Cas ignored Dean’s questioning look. With light touches, he brushed Dean’s matted hair out of his face. It was meant to be comforting, but if anything, it just worried Dean more. 

An advanced terminal illness. That’s what the test results said. 

Those four words ruined Dean and Cas’s life. Those four words unraveled years of plans the two had previously made, imagining they had all of the time in the world. Now he was told he would have two years if he was lucky. Dean’s doctors offered aggressive treatment to prolong the inevitable, but he denied it. He knows what that treatment does to patients. They’re violently ill, bed ridden, and spend most of their time imprisoned in hospitals. Dean wanted to spend the rest of his short life as himself, with Cas by his side.

It wasn’t something to easily become accustomed to. Cas was in denial in the beginning. He went about life as if nothing has changed, but at night he would hold onto Dean extra tight, with no intention of letting go. It went on like this for a few weeks, until Dean came home from visiting Sam for the weekend to find Cas sitting on the kitchen floor sobbing. Dean dropped his duffel bag and wrapped his arms around Cas. He held him close, kissing the top of his head, burying his nose into his boyfriend’s dark hair, memorizing his scent. His hand rubbed small circles on Cas’s back, knowing it comforts him. He nearly let out a humorless laugh at the thought that he was the one dying, but also the one doing the comforting. It was then that he realized Cas is the only that has to live without him. If it was Cas dying, Dean knew he’d be completely broken too.

After they both released the emotions they had been repressing, they actually felt a little better. Now that they accepted the inevitable, they could live each day to the fullest. Without further discussion, Dean and Cas quit their respective jobs to focus on living life in the now. Besides, that’s what emergency savings are for, right?

This brings Dean to where he is now. Sitting in the living room at three in the morning with a glass of bourbon, paper, and a pen. He could feel his health slowly deteriorating and he knew he was running out of time. Dean estimated he has about six months remaining. At night he’d close his eyes and be met with the image of a clock. It would start with the seconds slowly ticking by and then morph into something sinister. Suddenly it was a calendar, with pages tearing away and flying off until there was nothing left but blackness and silence. He’d wake in a cold sweat, with the constant reminder of the inevitable looming over his head. Dean shook his head, clearing the dark thoughts. He took a sip of his drink before focusing back on the task at hand.

  1. _Have breakfast in bed_
  2. _Stargaze until the sun rises_
  3. _Kiss in the rain_
  4. _Rent a beach house for the weekend_
  5. _Watch Sam graduate from law school_
  6. _Go on a road trip with a kickass playlist_
  7. _Get married_
  8. _Go skinny dipping_
  9. _Die loved_



Dean didn't realize he was crying until a tear his list, smudging some of his handwriting. There is still so much he wants to do, so much more he wants to see but deep down he knows he doesn't have the time for it. Hell, he doesn't even know if he has time for his list. But he's going to try. He looked back at a few items on the list and managed a small smile, _so much for not being a romantic._

Dean looked up as he heard some shuffling and the opening of a door. His eyes met a sleepy Cas, with his blue eyes bleary and hair ruffled more than usual. It's a sight he will never get sick of.

“Can’t sleep?” Cas asked quietly. Dean hummed in response, struggling to get his emotions in check. He hated this vulnerability that comes with the diagnosis. Making this list made him even more emotional and he knew that crying in front of Cas would only make things harder.

“Me neither,” Cas sighed, joining Dean on the couch. He leaned into his side, curling in to soak in his body heat. “I can never sleep very long without you next to me.”

Dean smiled at that and kissed Cas on the temple. Cas sighed contentedly before frowning as he sees the list in Dean’s hand. “Is that your bucket list?”

“Yeah, I figured since we have _some_ time, we should make the most of it, you know? And there’s a lot of things I’ll never get the chance to do, so I thought I’d make a list of the ones most important to me.”

Cas gingerly grabbed the list out of his hand and read through it, a sad smile on his face. “No backpacking across Europe?”

“I don’t think there’s time for a trip to Europe,” Dean mumbled. He and Cas always dreamed of backpacking across Europe since they were in college. They talked of romantic stops in Italy for the food, France for the champagne, Ireland for the Guinness and beautiful countryside, Scotland for the scotch, and so much more. Cas just nodded in response, swallowing the lump in his throat. He didn't want to think about the concept of time at the moment.

“What do you want to do first?” Cas asked, his voice cracking.

“Right now, all I want to do is go to bed with you.”

“Alright, then let’s go to bed,” He replied, grabbing Dean’s hand and leading him into the bedroom with a sly smile on his face.

The next morning Dean awoke with another headache. He wasn't surprised, it’s been happening a lot more often lately. He sat up and reached for the pill bottles on the table next to the bed and swallowed the numerous pills prescribed to him by his doctors to keep his symptoms under control. Forcing his legs out from under the warmth of the blankets, Dean got up to see what Cas was doing. While Dean always sleeps later than Cas, he usually stays in bed with him reading a book while waiting for Dean to wake. After all, Cas knows how much Dean hates waking up alone.

Just as Dean crossed the room to the door, he was met with Cas carrying a tray full of chocolate chip pancakes, eggs, a heaping pile of bacon and his usual cup of coffee.

“Cas…” Dean started, realizing what he is doing.

“Dean! You ruined it. To have breakfast in bed, you actually need to be _in bed_.” He pouted which caused Dean to laugh at his boyfriend. He quickly turned around and crawled back into their bed.

“We don’t have to do everything on the list right away, angel.” He retorted, pulling the warm blankets onto his lap. His voice came across softer than the joking manner he intended -- his gratefulness for Cas shone through the usual sarcastic façade. Cas chose to ignore the comment and set the tray on the middle of the bed, settling in next to him. “But thank you,” Dean added, giving Cas a kiss on the lips.

Cas smiled, his blue eyes impossibly bright in the early afternoon light. Dean sighed, staring as he admired Cas’s beauty. His tousled dark hair, sticking in all directions accompanied with the stubble that comes from not shaving for a few days. He’s dressed in one of Dean’s classic rock shirts and a pair of boxers, with the smell of coffee lingering on his breath. Dean smiled at him, bacon momentarily forgotten, only consumed by thoughts of _Cas._ When things get bad, he wants to remember this specific moment and how happy the two of them are. _‘When things get bad…’_ Dean ended that train of thought and shook himself out of his daze, turning his attention to his delicious breakfast instead.

**Notes for the Chapter:**

> Hi friends! I’m so excited to post my first Dean/Cas work! I’ve written in other fandoms before but I just can’t shake the finale so this is my coping mechanism. This fic is finished, totaling at about 15,000 words. I plan to post either weekly or twice a week, depending on the reception this gets. Please let me know what you think!


	2. Floating in a Most Peculiar Way

**Summary for the Chapter:**

> Dean and Cas cross another item off Dean's bucket list. Then smut ensues.

Days quickly turned into weeks as Dean and Cas continued to spend every day together. Some days they would stay in and watch old movies together and some days they venture out into the city, needing a change of scenery. It was now the end of September and quickly becoming bitterly cold. Earlier that day they drove into Lawrence to grab coffee from the quaint coffee shop where they had their first date.

They sipped their coffees by the large stone fireplace in the corner, and reminisced over a shared piece of coffee cake. It was nearly five years to the date that they started dating and it seemed a fitting way to celebrate. Dean still remembers exactly how he felt when he arrived and saw Cas through the large bay window. He arrived early and was sipping on a latte which left a little bit of foam on his upper lip. Dean grinned at that and his nerves were quickly replaced with complete adoration.

Dean and Cas first met freshman year of college. It was during welcome week at a forced mixer for all freshmen in their dorm. Dean was sipping on the sickly-sweet punch that was in desperate need of some whiskey to level it out when he inconspicuously made his way to where the aux cord was located. Just because he was forced to be at this party didn't mean he was stuck listening to today’s top hits.

When he was within sight of the aux, he noticed that someone else beat him there. It was the most attractive man he had ever seen. With striking blue eyes that were in perfect contrast to his dark sex hair, he was like Dean’s biggest fantasy in the flesh. His eyes appreciatively roamed Cas’s body noticing the way his dark jeans clung to his thighs and the way his dark t-shirt stretched tight against his chest and arms.

Cas was furiously scrolling on the phone when suddenly the song changed. Space Oddity by David Bowie was now blasting through the speakers. He looked immediately pleased with himself and continued scrolling, adding more songs to the new queue of the playlist.

“You know, if you’re going to try and get away with changing the playlist, you should really pick a faster song to make it less obvious,” Dean mused.

Cas jumped, unaware that he was spotted changing the music. He quickly regained his composure and smiled crookedly. “Bowie is always the exception.” His voice was gravelly and deep and _holy hell_ he really was the hottest guy Dean had ever met.

Dean smiled at that. “I would say I’d drink to that, but this punch is certainly missing its kick.”

“You know, I think I can help with that.” Cas reached into his back pocket with an eyebrow raised and pulled out a silver flask. Glancing over his shoulder, he poured a healthy amount in Dean’s cup.

Dean took a long drink from the now significantly improved punch and grinned. “My god, and a whiskey drinker, nonetheless. Where have you been all my life?”

“Iowa,” Cas deadpanned.

Dean laughed and took another long drink of the punch.

“Want to get out of here?” Cas asked. “Go somewhere quieter, I mean. This isn’t really my scene.”

Dean grinned and raced out of the party with Cas in tow.

That night Dean and Cas walked along the deserted campus, passing the flask back and forth. They took turns being mock appalled over the bands the other hasn’t listened to, or the movies that haven’t been seen. They made future plans to correct those oversights and Dean felt true happiness for the first time in much too long.

Dean never kissed Cas that night. In fact, Dean didn’t kiss Cas until years after that night. They became comfortable in their friendship and Dean didn’t want to risk what they had. Cas ended up transferring back to Iowa for his last year of college to be close to his family when his mom was sick. After she passed, he moved back to Lawrence and it was through the late-night comfort sessions where Dean’s hands lingered too long, and Cas gripped Dean too tight that their friendship suddenly became so much more.

Dean was determined to do it right, so he asked Cas out on an official date and they went to their favorite coffee shop where they previously spent hours studying together. But this time, Dean could stare at Cas without worrying about the implications. He could reach out and touch him without trying to make up some excuse for it. It was freeing and exhilarating all at once. And now, five years after that first date, Cas still has that same impact on Dean.

It was those moments that Dean and Cas reminisced over in the coffee shop. Except there was an underlying tone of sadness and uncertainty for the future. But Dean pushed that away and focused on those happy memories. He focused on _Cas_ and found himself just as stupidly in love with him as that first day he met him.

Now Dean and Cas were back at their apartment, cuddled on the couch with coffee for Dean and hot chocolate for Cas. Dean was exhausted from their excursion. His fatigue was really setting in now. He had felt it earlier, beginning to weigh him down like a blanket. He refused to let the illness win today. Cas deserved a nice day. But now that he was laying on the couch with his head resting on Cas’s chest, he just didn’t have the strength to fight it anymore.

He was drifting into a blissful sleep when Cas nudged him. Dean grumbled and chose to ignore whatever the reason Cas was trying to wake him and relaxed, feeling sleep win over once again. Once again it was interrupted. “Jesus, _what is it_ Cas?”

“It’s raining,” He whispered, his mouth close to Dean’s ear.

“So?”

“So…it’s _raining,_ Dean.” The emphasis he put on it woke Dean as he shot up, staring at Cas with a smile on his face.

“It’s raining! We can cross number three off the list!”

It wasn’t that rain was uncommon in Kansas. In fact, there is probably quite a few rainy days left before it turns into snow, but Dean wanted to finish his list and he wants to experience the items while he can thoroughly enjoy them.

All signs of fatigue washed away from Dean and he leaped off the couch, bringing Cas with him. They both threw on rain jackets and some boots before bounding down the stairs. He felt like a kid again.

It was a cold rain, not the warm rain showers they had grown accustomed to throughout the summer. But Dean preferred this kind; the water refreshing and the goosebumps that form from it remind him that he is _alive._ Dean lifted his face towards the sky, feeling the raindrops wash over him. He opened his mouth to catch a few stray drops, laughing to himself because he used to do the same as a kid. When was the last time he enjoyed the rain? When was the last time that he wasn’t rushing to get out of it or complaining about the inconvenience of it? The answer is too long. He needed to focus on slowing down and enjoying life. And that’s what his list was all about.

Cas grabbed Dean’s hand breaking his train of thought and dragged him through a large puddle in the street outside their apartment. Dean smiled at his boyfriend, with his dark hair that was curling at the ends from the moisture and his pink lips that were beginning to turn a light shade of blue from the cold. He's truly beautiful. Cas wrapped his arm around Dean’s waist and pulled him against his chest, grabbing his other hand.

“May I have this dance?” Cas questioned, his mouth close to Dean’s ear which causes him to shiver and creates a wake of goosebumps of their own kind.

“Cas, you fucking sap,” Dean teased, but rests his head against his boyfriend’s shoulder nonetheless. They slowly pivoted in the middle of the street, the cold rain falling against them, soaking through their jackets and into their boots but none of that mattered. Not when they had each other by their sides. Dean sighed happily. Maybe he should have added ‘dance in the rain’ to his list because this – _this wa_ s absolutely perfect.

It wasn’t long before the cold rain seeped into what felt like their bones, and they stopped dancing. They both were lost in their own thoughts, but when they looked at each other, green eyes meeting blue, their thoughts quickly became consumed of the other. Dean glanced down to Cas’s lips and Cas rested his hand on the back of Dean’s neck, pulling him close.

The rain was cold, but their lips were warm, sending sparks of electricity through the other. Dean’s hands were on each side of Cas’s face as their mouths mesh together perfectly and leisurely. No wonder kissing in the rain was always romanticized in the movies. It's incredible. They kissed slowly and with meaning, pouring emotions into the kiss that neither can put into words. All thoughts of a bucket list, terminal illness, and the cold were quickly erased from Dean’s mind. Instead, all thoughts were of Cas. Dean deepened the kiss, running his tongue along Cas’s bottom lip, tasting him. He pressed his body against him, suddenly wanting – no, needing more of Cas.

A bright flash of lightning strikes, causing the two of them to jump apart, laughing at the other’s momentarily frightened expression.

“Come on,” Cas said, grabbing Dean’s hand once again. “Let’s go take a hot shower and we can continue where we left off.” Dean grinned and allowed Cas to lead him inside and upstairs to the warmth of their apartment.

It wasn't long before they were shut in the bathroom, stripping each other of their wet clothes as the water heats up. What originally started as a frenzy turned into something much more languid. Cas peeled Dean’s soaked shirt off of him and left a trail of kisses in its place which blaze into Dean’s skin. Cas kissed along his neck, lightly sucking and nibbling on the spot just under Dean’s ear that always elicits the sexiest sounds. When he was pleased with the mark he made, Cas continued down to his shoulders. He pressed feather light kisses along his muscles, paying extra attention to his collar bones.

Cas’s fingertips lightly brushed Dean’s nipple, to which Dean whines in response. “ _Cas.”_

“Patience,” He teased. Cas slipped his fingertips under the waistband of Dean’s boxers all while peppering kisses and licking along his broad chest. He ran his fingers along the soft skin and listened to Dean’s labored breathing. “Shower. Now.” Cas ordered, pushing his hands down and completely stripping Dean of his clothes.

They both stepped into the shower, letting the hot water wash over their chilled bodies. Dean raised his face towards the water, mimicking his earlier action in the rain. The hot water trickles down his body, washing away any remaining chill. Meanwhile, Cas grabbed a rag and soaps it up. He rubbed it in small circles along Dean’s back, massaging where he carries the most of his tension. “Cas,” Dean moaned. “Fuck, that feels so good.”

Cas hummed in response and leans against Dean’s back, pressing his erection against him. His hands moved to his front, gently moving along Dean’s chest and stomach, leaving soapy suds in its place. Dean let out a low moan in response to the gentle caresses and the feeling of Cas pressed against his ass. Cas’s hand moved lower, gripping Dean’s cock. He gently moved his hand along Dean’s hard length, jerking him off at a slow enough pace to drive Dean crazy. Dean whined in response; he can already feel the heat gathering in his stomach. “Cas, _please.”_

“Tell me what you want, Dean.”

“You,” He choked out. “Please. I want to feel you.”

Cas moaned and removed his hand from Dean. Dean nearly whimpered in response to the loss but then he heard the click of the lube bottle opening. Cas spread Dean’s legs and slicked up his fingers. He slowly pushed the first one past the tight ring of muscles. Dean groaned at the sensation and wiggled his hips against Cas, urging him to move. Cas gripped Dean’s hips with his free hand, stilling his movements as he inserts a second finger.

Cas paused, giving Dean a moment to adjust before he scissored his fingers, readying Dean for him. “ _Castiel_ ,” Dean hissed as Cas brushes his fingertip against his prostate. “C’mon, fuck, I need more.”

Cas chuckled at his boyfriend’s impatience and adds a third finger. He slowly slid them in and out, feeling the warm heat of Dean. Once Dean was ready, he removed his fingers and squirted more lube into his hand. He ran his hand along his own leaking cock. Dean looked over his shoulder and nearly came at the sight of Cas touching himself. His head was thrown back, eyebrows furrowed, and lips parted open.

“ _Dean,”_ Cas sighed as he removes his hand. He smirked at his boyfriend’s lust ridden expression. His pupils were dilated, leaving just a small ring of color around them. 

Cas pressed the tip of his cock against Dean’s hole, lightly teasing him. “Fuck, Cas. Just fucking take me already,” He growled. With that, Cas slowly pushed in, letting the tight ring of his muscles surround him.

“You’re so fucking tight, Dean.” He rasps, his voice now completely shot.

Dean wiggled his hips in response, letting Cas know it's okay to move now that he adjusted to the feeling of Cas inside him. He began pumping in and out at a slow pace, letting the tension slowly build. He adjusted his angle and brushed against Dean’s prostate on nearly every thrust.

“Cas, I need more,” He whimpered. Cas picked up the pace and began to kiss the crook of his neck. His breath was hot but it still left goosebumps in its wake.

Cas whispered into Dean’s ear, “Touch yourself.” Dean immediately did and began pumping his cock in time with Cas’s thrusts. It didn't take long until that heat was ready to bubble over. He knew Cas wasn't far behind based off the whimpers and curses tumbling from his lips. Cas picked up the pace, slamming into Dean’s prostate and Dean’s vision went white from the intense pleasure. “Cas!” He screamed as he spills over onto his hand and the shower wall.

As Dean expected, Cas was not far behind. It's a few more thrusts before he is following Dean off the edge with the cry of his name. The two of them caught their breath and quickly cleaned themselves up. Dean shut the water off and wrapped Cas up in a towel. He pulled him in and gently kisses him, inhaling the scent of his coconut conditioner.

“I love you so much, Cas.”

Cas grinned and replied, “And I love you more, Dean.”

Dean noted Cas’s look of pure adoration which made him feel warm and fuzzy on the inside. “Let’s go to bed, angel.” He mumbles with another quick kiss.

Within minutes they're tangled up together in bed, sound asleep. 

**Notes for the Chapter:**

> I wanted to add chapter 2 right away because I realized Chapter 1 didn't give as much of a glimpse into the story as I would like. Anyway, please let me know what you think! Bonus points if you can name the song the chapter title is based off :)


	3. Ramble On

**Summary for the Chapter:**

> Dean and Cas cross another item off Dean's bucket list by embarking on a road trip for Sam's law school graduation.

“Can you believe it? Sam Winchester: attorney at law.” Dean mused.

“Or Sam Winchester, Esquire.” Cas offered.

Dean snorted and shook his head, throwing another flannel in his suitcase. “He’s a big fancy lawyer now. My baby brother is all grown up.”

“Well, he _is_ twenty-seven. I imagine he’s been ‘all grown up’ for some time now,” Cas joked.

“Yeah, I suppose when he married Jess that ship kind of sailed, huh?”

“I suppose.” Cas agreed with a faint smile. He zipped his suitcase and sat on their bed, watching Dean throw another wrinkled shirt in his bag. “Are you really not going to fold that?”

Dean rolled his eyes. “Cas. It’s a t-shirt. I think it will be fine.”

“What about your nice shirt for his graduation?” He eyed Dean and took in the way he avoided meeting his eyes. “Please tell me you’re packing a nice shirt for his graduation.”

“It’s a graduation ceremony, Cas! I don’t need a suit. Remember his college graduation? Most people were dressed casually.”

“And remember when Jess booked us all a reservation at that French restaurant afterward? The host made you go home and change because you didn’t meet the dress code. Besides, I’m willing to bet Jess will make another fancy reservation for celebrations after the ceremony.”

“Okay, okay. I’ll bring a nice button-down. But I’m not wearing a suit,” He warned.

Cas held his hands up in mock surrender. “I would never dream of making you wear one.”

Dean threw the nearest button-down on the top of his suitcase and began zipping it up. He only paused when he heard Cas wince.

“It’s going _to wrinkle_ , Dean!”

Dean stepped back and scratched his jaw, letting out a sigh. “Okay, new plan: I’ll leave the room and make us some dinner. This allows you to completely repack _my_ suitcase the way _you_ like, and I won’t even complain about it.” 

Cas grinned, happy with the outcome. “Deal!”

Dean kissed the top of his head and left the room, mumbling something about how a few wrinkles wouldn’t hurt anyone, which Cas pointedly chose to ignore. He then dumped out the contents of Dean’s suitcase and methodically began folding and repacking the luggage.

As predicted, autumn was fleeting and quickly turned into a cold and brutal winter. It was only early December, but the wind was biting and the snow ruthless. When Dean and Cas learned that Sam was graduating from law school a semester early, they were ecstatic. Mostly because Sam was the male equivalent of Elle Woods by graduating from law school top of his class, but also because they get to trade the incessant cold of Kansas for the sunny warmth of California.

The timing of his graduation was perfect, actually. Dean’s symptoms remained stagnant for the last two months and were completely manageable with the help of his medications. If Sam hadn’t taken those extra summer classes the last two years, he would actually be graduating in May and Cas wasn’t so sure if Dean could make that cross-country trek six months from now. But he pushed that thought from his mind and returned to the task at hand.

They originally planned on flying to California for the graduation, but then Cas had a stroke of genius. Remembering item six on Dean’s list, he suggested turning it into a road trip. For as long as Cas has known him, Dean dreamed of road tripping along the historic Route 66, which begins in Chicago and ends in Los Angeles; and suddenly all of the pieces fit into place. They would join Route 66 in Oklahoma, just four hours away from Lawrence. Then they’d follow the route all the way to L.A., arriving just in time for Sam’s graduation from UCLA. After he proposed the idea, Dean was completely on board and already mapping out the best stops for pie and burgers along the way. 

Cas finished with Dean’s suitcase and quickly returned his attention back to his own bag. He double-checked he had everything packed, including a small wooden box hidden at the bottom with a certain piece of jewelry inside. Satisfied with the completion of his mental checklist, Cas zipped the bags and followed the scent of dinner to the kitchen.

“ _Dean.”_ Cas groaned, his voice rough and gravelly from sleep. “Must we leave at such an obscene hour?”

Dean chuckled and shut his car door. “According to the schedule that _you_ made, we need to drive about twelve hours today to make it on time. I’m just following your orders, babe.”

“The sun isn’t even up yet,” Cas whined, slumping in the seat.

“Here, this will help.” Dean handed him a large thermos with coffee and started the engine. The engine purred beneath him and Dean couldn’t help but let out a quiet sigh. It always felt so good to get behind the wheel of his baby. He put the car into gear and pulled out of their driveway, heading towards the open road.

He glanced over at Cas as he took a large gulp of coffee. His hair was sticking out in all directions, making it clear Cas didn’t even attempt to smooth it down today. He smiled at the grumpy expression on Cas’s face and turned his attention back to the road, drumming his fingers on the wheel.

The first hour of the drive was quiet. They headed south to hop onto Route 66 in Oklahoma. While they weren’t making the official Route 66 trek by beginning in Chicago, Dean was completely fine with that. He’d spent most of his life in the Midwest, he didn’t need to backtrack just to see the flat landscape he was already familiar with. The radio was playing softly as Dean and Cas both took the time to wake up for the day. As Cas pointed out, it was still dark so there were few cars on the road. It was actually a rather peaceful start to the day. 

As soft colors began to replace the dark sky, Cas’s mood began to turn around as the caffeine entered his system. He hummed along with the radio and watched the snow-covered trees quickly pass by. The pastel pinks and oranges from the rising sun reflected off the white snow, creating a warm glow. At that thought, he turned and leaned his back against the passenger door so he was facing Dean.

“You know, at first I was disappointed with the timing of the road trip. I didn’t think the drive would be very picturesque in December. I always thought fall or summer would be the opportune time to go.” He paused, looking back out the window. “But this is actually really nice. Everything is so still and quiet.”

“Well, by the time we get farther west it will feel like summer anyway. So, we’ll get a little bit of both.”

“That’s true,” Cas mused. “We should have done a road trip like this a long time ago.”

“We were always too busy with life. You had summers off, but that’s when the shop got the busiest for me. We just never made the time to slow down and experience things like this.” Dean observed. “Not that being so busy was a bad thing. We both loved our jobs, but we always said, ‘there will be a better time’ or ‘maybe next year.’ But now…well we don’t really have that privilege, do we?”

“I suppose not,” Cas sighed sadly.

“On a positive note, I’m glad that _now_ we’re making the time for things like this.”

“Me, too.” He murmured, attempting a smile.

“Hey,” Dean said softly. “Stop that.”

“Sorry, I don’t like thinking about how we can no longer make long-term plans.”

“Then don’t think about it.”

“You know it’s not that easy.”

“Yeah, yeah I get it. But right now, I’m here, okay?” Dean tore a hand away from the steering wheel and intertwined it with Cas’s. “Focus on that. When your mind starts wandering to those thoughts, shut it down and focus on the now. Because these moments right here, these are the ones I want you to look back on and I only want you to remember how happy we are. I don’t want this last year tainted with sadness. Can you do that for me?”

Cas nodded and squeezed Dean’s hand. The gesture said more than he could vocalize at the moment. Cas had never cared for anyone as much he does for Dean. He always thought that finding Dean and experiencing that all-consuming, world-shattering love with him was like some kind of reward for surviving the first shitty eighteen years of his life. But now that Cas knows their time together is limited, he can’t help but feel like the punchline to some kind of cosmic joke.

He shook his head and slowly exhaled, turning his attention on Dean’s advice to focus on the positives. Dean is next to him right now and that’s all that matters. He has his left hand draped on the steering wheel with his right intertwined with Cas’s; and despite the heavy conversation, he still has a genuine smile on his face. It’s the kind of smile that lights up his whole face, giving him a youthful glow regardless of the crinkles at the corners of his eyes. Cas returned his smile with a genuine one this time.

“We’re doing this all wrong, you know.” Cas states, changing the subject.

“Doing what wrong?” Dan asks quizzically.

“Your bucket list item. It said, ‘road trip with a kickass playlist.’ We’re currently road-tripping listening to a subpar radio station. Not really the same thing.”

“No,” He agreed. “I suppose it isn’t the same thing. Grab a tape out of the glove box, will ya?”

“I know you have very strict rules which state that the driver picks the music, but you’ll have to make an exception for this one instance.” Cas held up a cassette tape he dug out of his own jacket pocket which read _‘Dean’s Top 13 Zepp Traxx.’_

Dean grinned. “That is always an exception. Pop it in.”

He inserted the tape into the player and turned the volume up a little higher. The opening notes to _Immigrant Song_ played out and Cas settled into his seat, letting the music wash over him.

“Remember when I gave this to you?” Dean baited.

“We were fighting,” Cas laughed.

“Over something stupid.”

“Big surprise there.”

“God, I don’t even remember what the fight was about anymore.”

“I do. You –” Cas caught himself off. “You know what, it doesn’t matter.”

“Good save, Cas.”

Cas smirked. “You hadn’t talked to me all day. I was reading in the living room and you stomped in, dropped it on my lap and just walked away.”

“This was early in our relationship. I was bad at communicating! This was the best way I could tell you I was an idiot and that I was sorry.”

“Well, it obviously worked. I went for a drive and listened to it. I forgave you by the time this first song was over.”

“It’s only a two-minute song, Cas.”

“Exactly my point. I never have much resolve when it comes to staying mad at you, do I?”

“I suppose not,” Dean acknowledged. “Besides, that was a pretty romantic move on my part.”

“Yes, it was. If I hadn’t already been so in love with you at that point, I’m sure the mixtape would have sealed that deal.”

“So, what you’re saying is I should have made you a mixtape right after I met you?”

“I’m pretty sure from the moment I met you, I knew you were someone special, Dean.”

Dean flushed at that statement and he felt the tips of his ears turn pink. At this point in their relationship, he’d grown accustomed to how forward Cas can be, but it still has quite an impact on him. “Yeah, I thought the same about you,” He murmured.

Cas beamed at him, showing the whites of his teeth and leaned over to plant a quick kiss on his cheek. At that exact moment, the song ended and switched into _Good Times Bad Times_. Dean cranked it up and sang loudly along with Cas.

_I know what it means to be alone_

_I sure do wish I was at home_

_I don't care what the neighbors say_

_I'm gonna love you each and every day_

_You can feel the beat within my heart_

_Realize, sweet babe, we ain't ever gonna part_

Yeah, this moment here is the exact reason he put this item on his bucket list.

In no time, they were cruising on Route 66 heading west towards New Mexico, their destination for the night. When they stopped to grab gas and snacks a few miles back, Cas grabbed a handful of Route 66 brochures and had been thoughtfully studying them ever since.

“Anything good?” Dean asked, rather amused at his boyfriend’s total infatuation with the tourist gimmick.

“Did you know that Route 66 was commissioned in 1926 but wasn’t fully paved until 1938? Then in 1985, it was decertified a U.S. highway. Originally it was 2,448 miles in 1926 but now it totals 2,278 miles from beginning to end.”

Dean hummed in response, not daring to interrupt Cas. He learned it’s best to let Cas get it out of his system.

“You know, there’s a place called ‘Cadillac Ranch’ in Texas. We could stop there! We’re pretty close.” He chirped, bringing Dean’s attention back to the conversation.

“A Cadillac ranch?” Dean grimaced. “What is that?”

“It’s a public art sculpture of ten Cadillac’s buried nose-first in the ground.” Cas paused for a moment. “Actually, that doesn’t sound very appealing at all.”

Dean chuckled. “Thank God. I was wondering how I was going to talk you out of it.”

“Are there any stops along the way you want to make?”

“Cas, I’m in this for the driving and for the company. I don’t need to stop at niche tourist stops unless it’s something you really want to do.”

“I just want to make sure you get the full road trip experience!”

“To me, the full road trip experience is exactly what we got going: good music, good conversation, and my car. I don’t need anything else; I promise.”

“If you say so,” Cas’s lips turned up at the corner, in a smile that Dean recognized as pure contentment.

The rest of their drive sped by as they joked, sang along to the music, and reminisced as songs played that reminded them of different points in their lives. Soon enough, they were pulling into Santa Rosa, New Mexico where they decided to call it for a night. They found a mediocre chain hotel with vacancy and pulled off the road. At that point they had been in the car for a little over twelve hours and were in desperate need of some space to stretch out. Driving long distances used to be much easier. Now Dean’s joints popped as he stepped out of the Impala and his legs felt uncomfortably stiff.

Dean checked them in as Cas went to grab dinner. The original plan was to grab food and drinks to celebrate a successful first day, but Dean could feel the exhaustion weighing him down. So, Cas volunteered to pick up takeout instead. After throwing his and Cas’s bags down on the floor, Dean collapsed on the bed. Instantly he longed for his memory foam as the springs of the cheap mattress poked against his back. Truthfully, he wasn’t sure it would be a big enough problem to keep him awake as he was so damn tired.

As he was beginning to nod off, he heard the door to the room click open and was met with the intoxicating smell of greasy takeout. 

“Honey, I’m home!” Cas greeted cheerfully. “And I brought pie.”

Dean shot up from his spot on the bed and kissed Cas in thanks. “God, I love you.”

“Are you talking to me or the food?”

“Why not both?” He asked, his mouth already full of fries.

“Touché.” Cas laughed and began digging in as well. He joined Dean on the bed, with their knees touching as he flipped on the television and found a movie for them to watch. They ate in a peaceful quiet, both engrossed in the movie.

Once the food was gone and the slices of pie were eaten, they both began tiredly stripping down to their boxers.

Dean watched with a different form of hunger in his eyes as Cas undressed.

“I can feel you watching me.” He chided, bending over to put his discarded clothes back in his bag.

“Of course, I am. I have a sexy boyfriend who is undressing right in front of me,” He murmured, wrapping his arms around Cas. Cas leaned back into the touch, letting out a soft sigh. Dean began peppering kisses along Cas’s jaw, pausing only to suck on the sensitive spot below his ear. Cas let out a quiet whimper at that and closed his eyes. Dean continued kissing down his neck to his shoulders when he paused to fight a yawn breaking to the surface. 

Cas laughed and the tension immediately lifted. “C’mon, let’s go to bed.”

“I don’t wanna,” Dean grumbled. Yet he allowed himself to be pulled to bed anyway.

“You can have your way with me tomorrow, I promise. But for now, sleep.”

Dean hummed and pulled Cas’s arm around his waist, so they were spooning. All previous annoyances about the crappy mattress were pushed from his head and quickly replaced with thoughts of Cas as he felt a soft kiss press to the back of his neck. With that, he allowed himself to lose consciousness and fall into a deep, happy sleep.

**Notes for the Chapter:**

> Surprise, I decided to post the chapter two days early! Originally I planned on the whole road trip and Sam's graduation taking place in one chapter but it's turning out to be much longer than I anticipated. So I'll be breaking it up over the next chapter or two.
> 
> I also decided to change Sam's law school from Stanford to UCLA for the purpose of the road trip because Stanford would have been another 5 hours from L.A. and this just made it less complicated. 
> 
> Next chapter you can expect some smut, more road-tripping shenanigans and Sam! Please let me know what you think so far!


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